SML1456

Thaxtomin A

≥98% (HPLC)

• Synonym(s): (3R,6S)-3-Hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-2,5-piperazinedione, Thaxtomine A
• Empirical Formula (Hill Notation): C₂₂H₂₂N₄O₆
• CAS Number: 122380-18-1
• Molecular Weight: 438.43
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825893
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• color: yellow to orange
• storage temp.: −20°C
• SMILES string: O=C(N(C)[C@@H]1CC2=CNC3=C2C([N+]([O-])=O)=CC=C3)[C@@](CC4=CC(O)=CC=C4)(O)N(C)C1=O
• InChI: 1S/C22H22N4O6/c1-24-18(10-14-12-23-16-7-4-8-17(19(14)16)26(31)32)20(28)25(2)22(30,21(24)29)11-13-5-3-6-15(27)9-13/h3-9,12,18,23,27,30H,10-11H2,1-2H3/t18-,22-/m1/s1
• InChI key: QRDNJYNIEGRRKV-XMSQKQJNSA-N

Description

General description

Thaxtomin A belongs to the class of 4-nitroindol-3-yl-containing 2,5 dioxopiperazines.

Biochem/physiol Actions

Cellulose synthesis inhibition by thaxtomin A, indicates plant-pathogen interaction. Along with this, it also results in hypocotyls swelling and decreased seedling growth. Thaxtomin A leads to common scab disease in potato. On the whole, it attenuates cell growth and induces cell death in the infected plant.

Thaxtomin A is a nitrated diketopiperazine phytotoxin produced by Streptomyces scabies that induces plant cells necrosis. Thaxtomin A is a potent plant cellulose synthesis inhibitor.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable